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It's easiest to put it in an end cap if your using a tire valve. If your using a threaded schrader then tap it into a fitting that has a pipe in it so that the schrader is in two layers and therefore more stable. If you can't get it through two layers oh well, it's not a huge problem. Just put a small nut in the inside of the pipe so the schrader can't pop out under pressure.

Rubber ones work, but yes, metal ones are the better choice. Here, the metal ones are 10 cents more but oh well. I just go to the bike shop and get all their busted tires for free if I want the rubber kind.